612-34-0

Usage

Uses

Used in Pharmaceutical Industry:
2-[(2-aminobenzoyl)amino]benzoic acid is used as a precursor in the synthesis of various pharmaceutical compounds for its versatile chemical properties and potential therapeutic applications.
Used in Skincare and Cosmetic Industry:
2-[(2-aminobenzoyl)amino]benzoic acid is used as an ingredient in skincare and cosmetic products for its antioxidant and anti-inflammatory properties, contributing to the development of formulations that promote skin health and protection.
Used in Food Industry:
2-[(2-aminobenzoyl)amino]benzoic acid is used as a flavoring agent in the food industry, particularly in the production of artificial flavors and fragrances, enhancing the sensory experience of food products.

InChI:InChI=1/C14H12N2O3/c15-11-7-3-1-5-9(11)13(17)16-12-8-4-2-6-10(12)14(18)19/h1-8H,15H2,(H,16,17)(H,18,19)

Upstream product

• 136918-14-4 phthalimide 
• 118-48-9 isatoic anhydride 
• 118-92-3 anthranilic acid 
• 1147-43-9 2-(2-aminobenzoyl)benzoic acid 
• 49854-16-2 methyl 2-(2-aminobenzoylamino)benzoate 
• 68506-37-6 2-(2-nitrobenzamido)benzoic acid 
• 7732-18-5 water 
• 7501-38-4 2-(2'-nitrophenyl)-3,1-benzoxazin-4-one 
• 64-19-7 acetic acid 
• 4005-06-5 2-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid 
• 64-17-5 ethanol 
• 228581-79-1 ethyl 2-(2-aminobenzoylamino)-benzoate 
• 37960-65-9 potassium anthranilate 
• 134-20-3 2-carbomethoxyaniline 

Downstream Products

• 49854-16-2 methyl 2-(2-aminobenzoylamino)benzoate 
• 25380-15-8 2-(4-oxo-4H-quinazolin-3-yl)benzoic acid 
• 118-92-3 anthranilic acid 
• 7265-24-9 2-(2'-amino-phenyl)-benzo[d][1,3]oxazin-4-one 
• 58426-37-2 2-[2-(acetylamino)benzoylamino]benzoic acid 
• 861527-11-9 2-(2-(phenylsulfonamido)benzamido)benzoic acid 
• 19577-93-6 N-(o-Methylaminobenzoyl)anthranilic acid 
• 96661-88-0 Mal-Ant-Ant 
• 101247-41-0 2-[2-(3,4-Dichloro-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-benzoylamino]-benzoic acid 
• 101247-52-3 N-<2-(N'-Anthranoyl-anthranoyl)-3-chlor-maleoyl>-α-aminobutyryl-glycin 
• 107469-44-3 2-(4-oxo-4H-benzo[d][1,2,3]triazin-3-yl)-benzoic acid 
• 116470-48-5 N-(o-Ethylaminobenzoyl)anthranilic acid 
• 457907-91-4 2-(2-dodecanoylamino-benzoylamino)-benzoic acid 
• 457907-96-9 2-(2-undec-10-enoylamino-benzoylamino)-benzoic acid 

Relevant academic research and scientific papers

Highly selective and sensitive long fluorescence lifetime polyurethane foam sensor based on Tb-complex as chromophore for the detection of H2PO4 ? in water

Developing novel rare-earth complexes to rapidly and reliably sensing anions in pure water is highly challenging. Here, a series of long fluorescence lifetime polyurethane foam bonded Tb(BAA)3 chromophore porous material (Tb-PUFs) have been designed and synthesized via a simple one-step co-polycondensation reaction as an efficient fluorescent sensor for H2PO4 ? in pure water. All Tb-PUFs exhibited strong green emission and long fluorescence lifetime in water, which was ascribed to Tb-complex can be dispersed very well in polyurethane foam, effectively avoiding the emission quenching of Tb3+ ions caused by water molecules vibration. The titration experimental results showed that precursor Tb(BAA)3 can effective recognize F?, CH3COO?, and H2PO4 ? in DMSO solution. Interestingly, Tb-PUFs can only selectively recognize H2PO4 ? in pure water, this phenomenon can be explained that H2PO4 ? is acidic, and can occur deprotonation with -NH group of ligand BAA, thus making the fluorescence quenching effect was more sensitive for H2PO4 ? in pure water. In addition, the sensing ability of Tb-PUFs for H2PO4 ? is highly reversible by washing them with deionized water for three times. In a word, all results implied that Tb-PUFs was an excellent candidate for H2PO4 ? ions detection selectively in pure water.

Unsymmetrically substituted dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A convenient scaffold for bioactive molecule design

A novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development.

Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists

Androgen receptor (AR) antagonists are used for hormone therapy of prostate cancer (PCa). However resistance to the treatment occurs eventually. One possible reason is the occurrence of AR mutations that prevent inhibition of AR-mediated transactivation by antagonists. To offer in future more options to inhibit AR signaling, novel chemical lead structures for new AR antagonists would be beneficial. Here we analyzed structure-activity relationships of a battery of 36 non-steroidal structural variants of methyl anthranilate including 23 synthesized compounds. We identified structural requirements that lead to more potent AR antagonists. Specific compounds inhibit the transactivation of wild-type AR as well as AR mutants that render treatment resistance to hydroxyflutamide, bicalutamide and the second-generation AR antagonist enzalutamide. This suggests a distinct mode of inhibiting the AR compared to the clinically used compounds. Competition assays suggest binding of these compounds to the AR ligand binding domain and inhibit PCa cell proliferation. Moreover, active compounds induce cellular senescence despite inhibition of AR-mediated transactivation indicating a transactivation-independent AR-pathway. In line with this, fluorescence resonance after photobleaching (FRAP) - assays reveal higher mobility of the AR in the cell nuclei. Mechanistically, fluorescence resonance energy transfer (FRET) - assays indicate that the amino-carboxy (N/C)-interaction of the AR is not affected, which is in contrast to known AR-antagonists. This suggests a mechanistically novel mode of AR-antagonism. Together, these findings indicate the identification of a novel chemical platform as a new lead structure that extends the diversity of known AR antagonists and possesses a distinct mode of antagonizing AR-function.

Rare-earth terbium complex, polyurethane foam doped with rare-earth terbium complex and application thereof

The invention provides a rare-earth terbium complex, polyurethane foam doped with the rare-earth terbium complex and application thereof. The rare-earth terbium complex has a molecular formula of Tb(BAA).2H2O. The polyurethane foam is prepared by the following steps: synthesizing an aminobenzoic acid derivative BAA by taking o-aminobenzoic acid and isatoic anhydride as main raw materials, performing coordination with TbCl3.6H2O according to a molar ratio of 3:1, synthesizing a terbium complex Tb(BAA).2H2O, and doping the terbium complex in polyurethane foam, thereby obtaining the polyurethane foam with the advantages of excellent luminescence property and high thermal stability. The rare-earth terbium complex and the polyurethane foam doped with the rare-earth terbium complex are used for detecting H2PO4, CH3COO and/or F. According to the rare-earth terbium complex and the polyurethane foam of the rare-earth terbium complex disclosed by the invention, the luminescence stability of terbium ions is improved, the luminescence lifetime is prolonged, the preparation cost is low, and the method is simple and easy to operate and has wide application prospects in the fields such as biological materials, medical treatment, agriculture, daily use chemicals and the like.

Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives

A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract: [Figure not available: see fulltext.]

Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones

Using scandium triflate and microwaves, the direct double dehydrocyclization of anthranilate-containing tripeptides was achieved, affording the total syntheses of (i) quinazolino[3,2-a]benzodiazepinediones (1a-f), (ii) diazepino[2,1-b]quinazolinediones (2a-e), and (iii) pyrazino[2,1-b]quinazolinediones (3a-e) with good overall isolated yields (23-43%, 37-47% and 31-56%, respectively). Among the quinazolino[3,2-a] benzodiazepinediones synthesized, 1a (sclerotigenin), 1b (circumdatin F), and 1f (asperlicin C) are natural products.

Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines

Using tin triflate, as an effective Lewis acid, and microwaves, direct double cyclizations of bis(anthranilate)-containing tripeptide precursors to afford the total syntheses of 7-substituted quinazolino[3,2-a][1,4] benzodiazepinediones (1a-f), including natural products circumdatin F (1a), sclerotigenin (1b), and asperlicin C (1c), were achieved with good overall isolated yields (23-62%). The Royal Society of Chemistry.

An efficient, convenient synthesis of novel medium-sized 13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione macrolides as anticipated antineoplastic agents

A series of novel medium-sized 13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione macrolides (18-27, 30, 32) were synthesized in an ongoing effort to develop new antineoplastic agents. The synthon 2-(2-aminobenzoylamino)-benzoic acid (7), for preparation of the target compounds, was prepared via the reaction of isatoic anhydride 5 and anthranilic acid 6. Nine compounds (18-20, 24-27, 30, 32) were subjected to National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay. Among the compounds tested, 6-benzyl-13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione (26, NSC 721327), bearing the benzyl group at position 6, showed cytotoxic activity and subpanel selectivity against leukemia (CCRF-CEM), colon (HCC-2998), CNS (SNB-75) and melanoma (UACC-257) panels at log10 GI50 (M), compound concentration that inhibits 50% of cell growth, ranging from -4.08 to -4.59.

Conformational Behaviour of Medium-sized Rings. Part 11. Dianthranilides and Trianthranilides

Two approaches to the stepwise syntheses of N,N'-di- and N,N',N''-tri-substituted trianthranilide derivatives (5)-(20) are described.In the shorter synthetic route, the key acyclic intermediate, N-anthranilic acid (26) is prepared in a stepwise manner from anthranilic acid, isatoic anhydride (23), followed by o-nitrobenzoyl chloride.Alkylations of the amide functions at nitrogen, reductions of the aromatic nitrogroups, and cyclisations of the acyclic amino-acid derivatives provide a direct route to N,N'-dimethyl- (5) and N,N'-dibenzyl- (14) trianthranilides.Further alkylations or acylations of either (5) or (14) afford (i) N,N',N''-trimethyltrianthranilide (7) and its trideuteriomethyl analogue (8), (ii) N,N'-dimethyl-N''-acetyl- (10), -N''-benzoyl- (11), and -N''-benzyl- (12) trianthranilides, (iii) N,N',N''-tribenzyltrianthranilide (15), and (iv) N,N'-dibenzyl-N''-methyltrianthranilide (16).In the longer synthetic route, the key acyclic intermediate, methyl N-methyl-N-anthranilate (42) is prepared in a stepwise manner from anthranilic acid and two molar equivalents of o-nitrobenzoyl chloride.Alkylations of the unsubstituted amide functions at nitrogen, reductions of the aromatic nitro-groups, and cyclisations of the acyclic amino-acid derivatives provide, not only an alternative route to N,N'-dimethyltrianthranilide (5) but also, a general route to the N-methyl-N'-trideuteriomethyl- (6), N-methyl-N'-benzyl- (17), and N-methyl-N'-ethyl- (19) analogues.Further alkylations of these N,N'-disubstituted derivatives afford N-methyl-N',N''-di(trideuteriomethyl)- (9), N-methyl-N'-trideuteriomethyl-N''-benzyl- (13), N-methyl-N'-benzyl-N''-ethyl- (18), and N-methyl-N'-ethyl-N''-benzyl- (20) trianthranilides.The constitutionally symmetrical N,N',N''-trimethyl- (7) and N,N',N''-tribenzyl- (15) trianthranilides exist in solution as an equilibrium mixture of propeller and helical conformations.In the case of the N,N',N''-trimethyl derivative (7), the predominant diastereoisomer with the helical conformation has been isolated as a pure compound.In the case of the N,N',N''-tribenzyl derivative (15), the propeller and helical conformational diastereoisomers have both been characterised as crystalline compounds.For both these compounds, the free-energy barriers to conformational inversion and interconversion processes in solution have been obtained from (i) direct equilibration experiments and (ii) dynamic 1H n.m.r. spectroscopy.Constitutionally unsymmetrical N,N'-di- and N,N',N''-tri-substituted trianthranilide derivatives can adopt three helical conformations in addition to a propeller conformation.Assignments have been made to conformations and conformational diastereoisomers of the N,N'-dimethyl- (5), N,N'-dimethyl-N''-benzyl- (12), N,N'-dibenzyl- (14), N,N'-dibenzyl-N''-methyl- (16), N-methyl-N'-benzyl- (17), N-methyl-N'-benzyl-N''-ethyl- ...